Add time:09/05/2019         Source:sciencedirect.com

C-linked disaccharide derivatives mimicking O-β-d-galactopyranosyl-(1→3)-d-galactopyranosides (end groups in Core-B structures of biologically important proteoglycans) have been obtained from isolevoglucosenone and β-d-galactopyranosylcarbaldehyde derivatives. The β-d-galactopyranosyl-(1→3)-CH(OH)-d-galactal derivatives 3a (4,6-di-O-acetyl-3-C-[(1R)-1,3,4,5,7-penta-O-acetyl-2,6-anhydro-d-glycero-l-manno-heptito1-1-C-yl]-3-deoxy-d-galactal), 3b (4,6-di-O-benzyl-3-C-[(1R)-2,6-anhydro-1,3,4,5,7-penta-O-benzyl-d-glycero-l-manno-heptitol-1-C-yl]-3-deoxy-d-galactal) and the β-d-galactopyranosyl-(1→3)-CH2-d-galactal 3c (4,6-O-diacetyl-3-C-) [6-O-acetyl-2,3,4-tri-O-(tert-butyl)dimethylsilyl-β-d-galactopyranosylmethyl]-3-deoxy-d-galactal have been prepared. One of them, 3a, has been shown to be a suitable agent for the O-glycosidation and the construction of glycoconjugates bearing the β-d-Galp-(1→3)-CH(OH)-d-Galp-O moiety.

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